During the past 40 years, the Philosophy for Children movement has developed a dialogical framework for education that has inspired people both inside and outside academia. This article concentrates on analysing the historical development in general and then taking a more rigorous look at the recent discourse of the movement. The analysis proceeds by examining the changes between the so-called first and second generation, which suggests that Philosophy for Children is adapting to a postmodern world by challenging the humanistic ideas of first-generation authors. A new understanding of childhood is presented by second-generation authors as giving possibilities for the subject to emerge in truly philosophical encounters. This article tries to show some of the possibilities and limits of such an understanding by considering the views in the light of general educational theorisations concerning pedagogical action. The continental tradition of European educational discourse, especially in the German-speaking regions, has stressed a necessity for asymmetry in the educational relationship. This line of thought is in conflict with the idea of a symmetrical, communal emergent system, which seems to be at the heart of second-generation understanding of educational philosophical dialoguing. The concluding argument states that in education we are always confronted with questions about purpose and aims, which have a special (educational) character in relation to pure philosophy/dialogue, although the philosophical/dialogical dimension is necessary for the emergence of unique subjectivity.